1: 74 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 2: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h 3: 61 percent / pyridinium p-toluenosulphonate / methanol / 6 h / 55 °C 4: 90 percent / H2, quinoline / Lindlar's catalyst / hexane 5: 80 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

pyridine; 4-(N,N-dimethlyamino)pyridine T=0°C; 0.333333 h;

1: 74 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 2: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h 3: 61 percent / pyridinium p-toluenosulphonate / methanol / 6 h / 55 °C View Scheme

1: 74 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 2: 1.) Mg, 2.) Li2CuCl4 / 1.) THF, -10 deg, 30 min, 2.) THF, -10 deg C, 3 h View Scheme

1: 1.) n-BuLi, Ph3CH, HMPTA, 2.) TsCl, 3.) NaBr 2: 1.) LDA, 2.) SiO2 / 1.) hexane, THF, HMPTA, 0 deg C, 45 min, 2.) hexane, THF, HMPTA. 0-25 deg C 3: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C 4: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C 5: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C View Scheme